First Thoughts On Tobin Leaving

John Tobin is leaving the Boston City Council, where he has represented District 6 (West Roxbury/Jamaica Plain) for nine years. Some quick thoughts and questions:

--Tobin's been a pretty solid councilor, particularly when it comes to constituent services -- and that's a district that expects a lot from its district councilor. He's also, in my opinion, generally done a good job balancing between the more conservative leanings of much of his district, and the more progressive direction of the city as a whole (and within his district).

--Tobin will be taking a top external-relations job at Northeastern University, where they'll be relying on his political skills to usher through their expansion plans and other issues. Seems like a good fit.

--Does this mark the end of Tobin's political career? Talking to him this morning, I got the sense that he doesn't think it necessarily does. But others I've spoken with think that it would be very hard for him to come back and run for Mayor, which has clearly been on his radar for years.

--With Tobin leaving, and with Marian Walsh retiring after 18 years in the state senate, one could conjecture that the West Roxbury area faces a decline in political power. Certainly you can't immediately replace the experience, influence, and institutional knowledge of Tobin and Walsh. But the power really comes from the fact that West Roxbury votes, and that hasn't changed. What this probably does accomplish is heightening the power of at-large councilor John Connolly, who now becomes the #1 powerholder on the parkway. Also worth considering: is there a power swing toward (light-voting) JP, home of new at-large councilor Felix Arroyo and state senator Sonia Chang-Diaz?

--Tobin will be replaced by special election, with a preliminary cutting the field to the top two, and then a final 30 days later. My sense at this point is that the preliminary will likely be after the regularly-scheduled state election -- perhaps with the prelim in late November.

--Matt O'Malley tells me that he is a candidate for that seat. O'Malley, currently field director for Steve Grossman's campaign for state Treasurer, has run twice for an at-large council seat. He says he already has the backing of Sheriff Andrea Cabral (whose campaign he previously managed), and Connolly. Expect MassEquality (where O'Malley briefly worked) to be on his side as well. O'Malley grew up in West Roxbury and has been very active there, and is now a homeowner in JP -- perhaps joining Arroyo and Chang-Diaz as a new JP power nexus?

--David Isberg, Tobin's chief of staff, is seriously considering running for the seat. Tobin says he will back Isberg if he runs. Insiders will inevitably talk about O'Malley-Isberg as a proxy battle between Connolly and Tobin for political king of the district.

--If the timing turns out as I suggest above, it would be possible for candidates currently running for state rep in West Roxbury (to replace Michael Rush, who is running for Walsh's senate seat) to enter the council race after losing the mid-September preliminary. That could include Kelly Tynan or Ed Coppinger. But that would put them well behind other candidates -- and in particular, would mean they come in after pols like Tobin and Connolly (who are backing Tynan and Coppinger, respectively, in the rep race) have attached themselves to other horses. It's also possible that one of them could drop out of the rep race to run for council instead.

--State rep Jeffrey Sanchez could run, but the suspicion is that he's doing too well moving up in the House right now to enter a race that could result in a humiliating loss. It's also possible that Jeffrey Herman, who is running against Sanchez, could switch races.

--Everyone expects someone to run out of the JP part of the district -- and in particular, a Hispanic candidate -- but so far I've got no names. The last time Tobin has an opponent, in 2005, Gibran Rivera beat him in the Ward 10, 11, and 19 districts (JP and bits of Roxbury and Roslindale), but Tobin crushed him in Ward 20, which is mostly West Roxbury, and which holds the bulk of the district's votes. A strong minority candidate, running against several candidates splitting the white suburban vote, could get to the runoff; but could they win the head-to-head?